


Headhunters

by deathtoonormalcy



Category: SPN, Supernatural
Genre: Alternate Universe, Crime, Crimeboss!Cas, Crossover, Hitman!Dean, M/M, Murder, Organized Crime, Prison, Serial Killers, Slutty!Cas, lawyer!Sam
Language: English
Status: In-Progress
Published: 2013-05-15
Updated: 2013-05-15
Packaged: 2017-12-11 22:27:45
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 2
Words: 4,114
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/803945
Author URL: https://archiveofourown.org/users/deathtoonormalcy/pseuds/deathtoonormalcy
Summary: <blockquote class="userstuff">
              <p>Sam Winchester has finally got his big break as a beginning lawyer. He's consulting on the case of Dean Moran, a psychotic hitman who had been all over the news when him and his boyfriend had wrecked havoc all over New York city. Dean gets all of the blame, while Sam tries to search for the truth. But Dean may still have feeling for the man who he claims to hate more than anyone else in the world. (Castiel is based on Moriarty; and Dean, Moran)</p>
            </blockquote>





	1. Chapter 1

**Headhunters**

~deathtoonormalcy~

 Sam hears his slightly too tight new leather shoes clack nosily against the grimy tile floors as he enters the prison.

He'd gotten a new suit, new shoes, and a haircut for this case. This could be the defining moment in his career as a lawyer. He needs to be at his best, but they hadn't had shoes his size and his haircut flips under his chin and makes him feel a little self conscious.

Tugging at his tie he glances at himself in a reflection off the glass on the door, the white blinds are drawn down. He raps his knuckles against the glass and shifts akwardly while he waits. The door creaks open and a broad man in a uniform looks up at him.

"You here for Moran?" The guard demands, looking annoyed. Sam feels himself nod shyly and scowls at himself, straighting his shoulders.

"I'm here to represent Dean Moran on his case." Sam blurts, having to resist brushing back his hair when it falls over his face. The guard lifts and eyebrow and opens the door wider, allowing him in. It's a small room. Two other guards are sitting in the front ofice area. Coffee cups littered on the table and thrown hazphardly towards the trashcan.

"He's in holding block thirteen." The officer states, pointing to a screen. The blurry black and white image shows a man turned to talk to a guard in a small square room.

"Thank you." Sam says, waiting for the guard to open the door. The loud screetch of metal grates over his ear as it unlocks.

"Good luck." One of the men say at his back, and the others laugh. Sam ignores them, following the long somewhat dimly lit hall for several minutes. The prison is heavily guarded. Sam passes several officers carrying large guns who ask to see his visitors pass. Finally he finds room thirteen. Two more men posted on either side of the door, stern frowns on their mouths.

They look wary when Sam approches.

"I'm Moran's lawyer." Sam says, annoyed with having to introduce himself several times just to see one man. He hopes it wasn't this difficult to get in contact with the convict for every one of his visits.

"Not for long." One of the men grunts, and the other snorts. Sam frowns at them, and steps through the door when one of them open it.

The room is dimly lit and has a simple metal table with little dings marking the smooth surface. Two chairs sit in the room, only one of them is free so Sam settles in it. Ignoring how it creaks under his dense weight.

"Who the fuck are you?" Sam finally looks up and studies the man sitting across from him. Dean Moran is as handsome as the newspapers had depicted him. Short dirty blonde hair sticking up messily, while his white teeth flash as he curls his lip in annoyance at a stranger in his territory.

"I'm Sam Winchester. I'm your lawyer." Sam reaches out to offer his hand but the guard standing behind Dean shakes his head. Sam drops his hand. Dean's wrists are bound with heavy chains connected to the table, as are his ankles.

"I told them to stop sending you fucks, I don't need no damn lawyer." Dean bites out, leaning back in his chair. Under his orange jumpsuit he is well built, with strong smooth muscles. He is a large man, not as large as Sam but then again not many are.

"I'm here to help you." Sam reasons, feeling annoyance prickle at the back of his neck as he tries to stay calm. Dean makes a rude noise, and eyes Sam up and down.

"I used to eat kids like you for breakfast." Dean mocks, bravado settling across him. Sam feels ripples of disgust well in him. Dean is a bully, and Sam hates bullies. But he needs this case.

"And look where it's landed you." Sam snaps back. This makes Dean blanch, anger forcing it's way over his face.

"I'm not in here because of anything I did! It's all C-" Dean's voice cuts off and he looks shocked at either himself or Sam, neither can tell.

"If I'm going to help you, you're going to have to tell me everything." Sam says, taking out his notebook and pen. Dean has very attractive eyes, Sam realizes. Even when they are narrowed in suspicion.

"I ain't telling you shit. You'll be gone in a week." Dean smirks, the way he's looking at Sam makes him feel small. But Sam won't back down, he's worked too hard and he won't be bullied into submission.

"I'm going to help you. Whether you like it or not." Sam says, letting his stubborn determination settle in his words. If Dean is surprised he doesn't show it, he just grits his teeth and glares.

* * *

For the first two weeks Sam visits Dean every other day. Moran is as stubborn as he is and refuses to even acknowledge his existence. Sam still does his research, research has always been something he's good at. Dean is loner. He hasn't aligned himself with any of the prison gangs and he has no friends other than the elderly prison janitor names Bobby.

Dean likes to make rude comments to the guards, harassing them until they attack him so he can get into the brawls he loves so much. The only way his superiors can get Dean to behave are through bribing him with classic rock cassettes to put into his ancient Walkman he keeps in his cell.

"Hey Samantha." Dean spits, as soon as he enters. Dean is even more hostile to him because he is forced into their nearly daily visits.

"Moran." Sam greets equally icily. He sets down the plastic container and Dean lifts his nose.

"If you're asking for my hand, the answer is no." He mocks with feigned disinterest. But clearly his curiosity is bubbling in him. Sam cracks open the container, letting the smell of a huge greasy bacon and cheese burger with a side of fries waft into the room. Dean's eyes practically melt as he reaches forward. Sam jerks the meal back.

"You give me answers, and I'll give you food. I bet mystery meat monday is getting a little old." Sam says, closing the container and settling it on his lap. Dean licks his lips, shifting in his chair.

"You really think after all this time, the thing that's gonna get me to break is gonna be a couple of french fries?" Dean asks, leaning back in his chair. Sam is sure that if his feet weren't chained to the floor he would have them crossed on the table top.

"No, but this might." Sam pulls out the newspaper clipping and sets it down in front of Dean. The black and white picture was taken yesterday, the man in the picture is around Sam's age. His dark curls are brushed back away from his face and he looks elegant in a dark tailored suit.

Another tall blonde haired man is leaning down to whisper something in his ear, and the smaller man is smiling smoothly.

Sam looks up and expects Dean to hide his reaction. But the white hot jealousy on his face is raw and intense.

" _Moriarty merges with Milton Inc_." Sam reads. Milton Inc was run by Balthazor and Anna Milton. Siblings who had half of the stocks in New York City under lock and key.

Now Castiel had them all.

Sam had been keeping tabs on the man. Castiel Moriarty was twenty eight years old. He had taken over his families vast business by the time he was twenty three. He had practically held an uprising, and taken out the competition brutally. When people called foul play they disappeared.

Castiel Moriarty was dangerous, and getting more powerful by the day.

Sam would wager that one of his key tools had been the man sitting in front of him, about to burst from how red he was going in anger.

"I understand that their is so-" Sam doesn't get a chance to finish his sentence. Dean is up and over the table, easily breaking the chain holding his cuffs to the table.

Sam chokes as he's caught around the neck.

"Who the fuck do you think you are, huh?! Showing em this shit?! I don't give a shit about him anymore! He can do whatever he fucking wants!" Dean's screaming in his face, Sam can hear his voice cracking in anger. He can see the betrayal in Dean's green eyes.

Sam realizes in the moment that Dean wasn't just one of Moriarty's loyal followers, he was in love with the criminal.

"I'm sorry." Sam chokes, voice catching. Dean releases him just before the guard can pull him off.

"I'm okay, let him be." Sam croaks, waving off the guards as they try and haul dean away. Dean settles back in the chair. Looking away. The air between them is tense, and

Sam slowly slides the burger across to Dean. Dean takes it and starts folding into the meal.

"Is Moriarty the reason you're in here?" Sam asks quietly, but the guards can probably hear from where they are hovering behind Dean. Dean doesn't look up from his burger, chewing loudly.

"I don't want to talk about it." Dean grits, shoving a hand full of fries into his mouth.

"I can help you get revenge, Dean. I can help you take him down." Sam promises, because he knows enough of Dean to know that Dean isn't a bad guy. Well, he isn't good either, but he doesn't deserve to take on all the crimes that Moriarty has done.

Sam is shocked when Dean pauses in his loud smacking.

"You can get me out of here?" Dean asks, voice so tiny and hopeful that Sam thinks that he sounds like a little boy that got lost. Sam very much wants to help him.

"I can." Sam promises. Dean swallows and looks away, he continues eating his meal.

"I'll give you some time to think about it. I'll be back tomorrow." Sam says, reaching across the table to take the newspaper clipping of Castiel and Balthazar. Dean's hand slams down over his.

"I'll keep this." Dean says, flushing darkly as he carefully folds the paper and tucks it into the pocket above his heart.


	2. Testimony

**Summary for the Chapter:**

> "I wasn't ... gay or anything. I mean, I'm still not. It's just, Cas. He has this sorta thing about him. Real seductive or something. I don't know how to explain it. He's like one of those mermaids that killed sailors-"
> 
> "A siren." Sam supplies.

Sam sits impatiently in the holding cell. Usually when he comes for his visits with Dean, the criminal is already waiting their for him. But today Dean isn't their to make his usual witty retorts. Sam gets up and goes to the door, he finds the nearest guard.

"Is Dean Moran on his way for his meeting with me?" Sam demands, glancing down at his his wristwatch. It's been nearly an hour of him sitting alone in the stuffy room. The guard blinks owlishly.

"Moran was put in solitary last night." The guard relays. Sam nods, biting back a curse as he storms down the hall. He finds the warden of the prison's office and knocks on the door.

"Come in." A nasally voice scratches. A large man, with beady little eyes looks up at him.

"Can I help you?" The warden asks, not even trying to hide his annoyance.

"I'm Sam Winchester, lawyer for Dean Moran. I've been waiting for almost an hour for our scheduled meeting, and I'd like to know why I wasn't informed that my client is having behaviral issues." Sam's voice is too sharp, he takes a calmy breath and schools his features.

The Warden's nameplate says his name is Zachariah Adler.

"Well Mr. Winchester, all you had to do was ask!" Adler spits with a slimy grin, getting up and going to a file cabinet. He fingers through until he pulls out a thick folder, slamming it down on the desk in front of Sam.

"Whats this?" Sam asks in confusion.

"You're clients list of behavioral issues since he's been here." Adler sneered.

"Dean's only been here for a year." Sam reasoned, brow furrowing as he opened the file. Complaints from guards and staff and other cell mates. Dean was more dangerous than Sam gave him credit for. He was incredibly resourceful and the first few months he'd been here he had made weapons from so many things that they had been forced to strip his cell down to a foam mattress with a blanket.

"He's improved." Sam insists. Dean had slowly gotten things back. He stopped trying to murder his guards and resorted to pacing like a caged dog instead of taking out his volatile energy on the staff.

"Slightly. He had a relapse last night. Nearly killed another prisoner." Adler grunted in annoyance, sitting heavily behind his desk.

"What happened?" Sam demanded, closing the file. He rubbed his forehead. Dean was going to be a very difficult case.

"He was looking at a newspaper or something and some idiot tried to take it from him, he beat his face in on the metal bench." Adler sighed, like the prisoners nearly dying where an inconvenience to him.

"I'd like to speak with him." Sam said, taking the file and holding it up.

"I'd also like a copy of this." Adler looks at him with his lips pursed.

* * *

"Sammy." Dean greets. Dean had been getting friendly during their latest visits. Only slightly, but it was still better than having the man choke him to death.

Sam sets down the thick file he had made a copy of.

"What's that?" Dean asks, digging into his ear with his finger. His cuffs rattle.

"A list of all of the problems you've caused since entering this prison." Sam watched Dean's eyes lit up.

"No way! Let me see." Dean grinned, flipping open the folder and laughing heartily at the first citation he read.

"Forgot about that one." He admits, turning to the next page. Sam scowls, pulling the file back.

"Dean, this kind of behavior is going to make it very difficult to plead your case to a judge." Sam explained, meeting Dean's green gaze. Dean shrugged, trying to cross his arms over his broad chest and failing due to the cuffs.

"I don't give a shit." Dean snapped, turning and looking away like a petulant child. Sam scrubs a hand over his face, just a few weeks ago Dean had asked for his help in getting free.

"You want to see him again, don't you?" Sam knows it's a low blow, but it's all he has. Dean's shoulders stiffen and he slowly meets Sam's gaze. Any of the childish immaturity has vanished and been replaced with pure rage.

"If I ever get out of here, first thing I'm gonna do is slit his throat." Dean snarls, eyes blazing. Sam swallows thickly at the threat. He should probably report it, but the world would be a better place without Castiel around. Dean would practically be doing a public service.

"Can you tell me how you met?" Sam asks carefully, like Dean's a frightened animal. Dean immediately locks down, eyes glazing over and he looks away. Unless he's spouting threats about Moriarty, he doesn't say much else.

"Dean, I need to know so I can help you." Sam presses. Dean's lips flatten into a think white line.

"Get lost." He tells the guard behind him. The guard blinks, realizing he's being spoken too.

"I'm not going anywhere, hot rod." The guard answers.

"This is a private conversation between me and my client." Sam says, staring the guard down until he slowly drifts from the room. He'll only be just outside of the door, but still.

Sam has never been alone with Dean, and he feels a pulse of nervousness crawl down his spine. Dean is dangerous and strong.

"What do you want to know?" Dean asks, toying with the metal links binding his hands together. He's looking down, brow creased.

"Everything."

"That's gonna take awhile." Dean pushes his fingers through his hair, and stares down at his lap as he begins his story.

* * *

When he lands in New York at the airport he's alone. No Mom or Dad waiting for him, not even a sibling or a girlfriend.

People are looking at him strange because of his uniform. Dean shoulders his bag and starts through the airport.

He doesn't even know why he told the deployer that he needed tickets to New York, he had lived in Kansas before he joined the military.

He'd been in the military since he was eighteen, he was twenty five now with a dishonorable discharge and fifty bucks to his name.

Dean ambled down the busy city streets, unsure what to do or where to go. He walked for a long time, until the sun set behind the vast climbing buildings that shrouded the city in darkness.

He found a bar and spent his fifty dollars on jack and tequila. The next day he woke up a few blocks from the bar, laying in a filthy alley with his head thankfully on cushioned on his military bag. Rolling onto his back he stares up at the sky, the fog from the early morning makes him cold.

"You pissed yourself." A raspy voice murmured somewhere above him. He tilted his head back and swore he saw an angel. The man had alabaster pale skin, paired with dark raven curls that brushed over the largest most beautiful clear eyes he'd ever seen. He feels the air punch of out his chest in a whoosh.

"I was drunk last night." Dean admits. Refusing to feel embarrassment in front of a stranger. The man squats down and looks at him curiously from upside down. Round blue eyes peer at him, the man is about six years younger than him, a boy still. He's holding his knees, and has a thick red scarf muffled around his neck. His lips are hidden behind it and his voice muffled.

"Really? I thought most homeless people wore military uniforms as their clothing of choice." The sarcasm was dry and Dean could feel his lips twisting up.

"You shouldn't talk to drunk strangers in alley ways, kid. Might get you in trouble." He warns the younger man, when the scarf slips down and reveals two plush chapped lips that are full and feminine. Dean finders himself staring.

"You're not a stranger," The boy touches his hair, smoothing it back from his forehead. His hands are warm and soft. Dean pushes up into them.

"I'm going to save you." The boy whispers.

* * *

"You met him in an alleyway?" Sam asks, he was carefully taking note. He had known that Dean had spent several years in the military. The news had broadcasted that almost accusingly.

"Yeah, he found me," Dean said, green eyes bland. He leaned forward on the table, staring down at it's surface as if he was lost in his blurry reflection.

"...he saved me..." Dean's voice was so low, Sam barely caught it.

"What?" He asked, because he thought he might have misheard.

"Nothing, you want to hear more, or are we done for the day?" Dean asks, already trying to stand up.

"No," Sam sounds panicked. Dean's emotional state was unstable, who knew how long it would be before he opened up like this again. Sam needed to get as much information as he could.

"Tell me more, what did you do afterward? You were homeless without a dime to your name." Sam asks, and he finds that even though he needs it for the case he is mildly curious.

"He took me to his dorms."

* * *

Dean smells like a toilet, but the strange boy doesn't seem to mind as he's led up the stairs in a fancy looking university. The sign had said it was the University of Leeds, which Dean had never heard of.

The dorm was big. With nice hardwood floors and a big living room. Papers and books where littered everywhere, a enormous bookcase rose against the wall, stacked with thick volumes. Dean spied a easel with a painting half finished on the balcony.

"My home." The boy smiled, full lips stretching over square white teeth.

"Why'd you bring me here?" Dean asked, setting down his bag and stretching. The warmth of the room brought feeling back into his muscles, the aches and pains started to settle in.

"Take a shower, I'll fix you something to eat." The boy turned, heading into the kitchen with a wave down the hall. Dean grabbed up his bag. He opened two wrong doors before finding the bathroom. He set the water to hot and scrubbed his skin clean.

Once he had changed and brushed his teeth clean of the lingering taste of alcohol; he went back into the living room, barefoot and sleepy.

"Eggs and toast." The boy presented, setting them on the small kitchen island that was also covered in papers and empty coffee mugs. Dean pushed them away to make a small space for himself to eat. He felt the kid watching him.

"You gonna tell me why I'm here?" Dean asked, this was beyond weird. He though maybe the kid was one of those bible thumpers who did goods deeds for the 'Lord', but he hadn't mentioned his 'heavenly father' yet.

"You needed help, and I wanted to help you." The boy shrugged, leaning forward and plucking one of Dean's toast up from his plate and taking a bite before depositing it back. It was strangely intimate to be sharing food with a stranger, even if was the strangers house and the strangers food.

"Look, I don't know what you want-" The kid cut him off.

"I don't want anything, Dean. You're company is enough." The boy smiled, removing his coat and scarf and setting it on a hook by the door. He was wearing a large knitted sweater than hung from his tiny shoulders. He had on dark trousers, and thick gray socks.

Dean stiffened slightly, eyes narrowing a fraction.

"People don't do stuff out of the charity of their hearts in my experience." Dean says, leaving his now empty plate and following the boy to the couch where he has stretched out. It's long enough where Dean can sit near his feet if he wants. But he chooses to stand.

"How insipid." Is the kid's only response and Dean doesn't know what that means. The kid sits up and leans forward to grab a book off his coffee table. Dean grabs him, easily lifting his smaller body back to his chest. He holds the hunting knife he had slipped from his bag to the boys throat.

A small broken gasp wrangles from between the boys lips, and Dean feels a pulse of arousal burn in his belly.

"Who are you?" Dean growls against his ear, digging the knife into his throat. The artery pulses strong and steady under the blade.

"This is how you introduce yourself to people?" The kid smiles, leaning back into Dean. He rests his head on Dean's shoulder, baring his pretty pale neck up submissively. Dean swallows thickly and tries no to get distracted.

"I didn't need to introduce myself, you already knew my name." Dean confronts. A pretty giggle spills from the boys lips.

"You're more observant than most." The kid's voice is sort of breathy, like he's pleased. He shifts against Dean, turning his face to push under Dean's jaw. Dean looses his hold a little and lets the boy nuzzle under him.

"Who are you." Dean repeats, voice drawn tight. He's trying to keep it together, but the kid is pushing up on his toes to get closer to him. Long black eyelashes fluttering against his flushed cheeks.

"Castiel Moriarty." The boy says, pressing his mouth against Dean's in a kiss.

* * *

"He just ... kissed you?" Sam asked, looking up at Dean with a raised brow. Dean nodded, looking away.

"I wasn't ... gay or anything. I mean, I'm still not. It's just, Cas. He has this sorta thing about him. Real seductive or something. I don't know how to explain it. He's like one of those mermaids that killed sailors-"

"A siren." Sam supplies.

"Yeah, like you can't resist. He lures you in. He's pretty good at getting what he wants, and he wanted me." Dean says, eyes bleary in memories.

"But not for long." Sam says, and he knows it's the wrong thing to say when Dean flinches hard. Dean's eyes are so sad, that Sam finds himself wanting to lean across the table and comfort the dangerous criminal.

"Not for long." Dean breathes, eyes closed in pain.


End file.
